Buchwald-Hartwig Amination of Coordinating Heterocycles Enabled by Large-but-Flexible Pd-BIAN-NHC Catalysts**

Dong Hui Li, Xiao Bing Lan, A. Xiang Song, Md Mahbubur Rahman, Chang Xu, Fei Dong Huang, Roman Szostak, Michal Szostak, Feng Shou Liu

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2 Scopus citations


A new class of large-but-flexible Pd-BIAN-NHC catalysts (BIAN=acenaphthoimidazolylidene, NHC=N-heterocyclic carbene) has been rationally designed to enable the challenging Buchwald-Hartwig amination of coordinating heterocycles. This robust class of BIAN-NHC catalysts permits cross-coupling under practical aerobic conditions of a variety of heterocycles with aryl, alkyl, and heteroarylamines, including historically challenging oxazoles and thiazoles as well as electron-deficient heterocycles containing multiple heteroatoms with BIAN-INon (N,N′-bis(2,6-di(4-heptyl)phenyl)-7H-acenaphtho[1,2-d]imidazol-8-ylidene) as the most effective ligand. Studies on the ligand structure and electronic properties of the carbene center are reported. The study should facilitate the discovery of even more active catalyst systems based on the unique BIAN-NHC scaffold.

Original languageEnglish (US)
Article numbere202103341
JournalChemistry - A European Journal
Issue number4
StatePublished - Jan 19 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry


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